Lithium amide → 3-Dimethylamino-5-(methylthio)benzo[b]thiophene-2-carboxamide

HRID 2226873Notes

Reaction equation

HRID 2226873 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[C:4]2[CH:15]=[C:14]([S:16][CH3:17])[CH:13]=[CH:12][C:5]=2[S:6][C:7]=1[C:8](OC)=[O:9].[NH2-:19].[Li+]>>[CH3:1][N:2]([CH3:18])[C:3]1[C:4]2[CH:15]=[C:14]([S:16][CH3:17])[CH:13]=[CH:12][C:5]=2[S:6][C:7]=1[C:8]([NH2:19])=[O:9]

Participants

3

Reactant 2

HCID 24532Lithium amideHCID 18963762Methyl 3-dimethylamino-5-(methylthio)benzo[b]thiophene-2-carboxylate

Product 1

HCID 189637763-Dimethylamino-5-(methylthio)benzo[b]thiophene-2-carboxamideYield 64%

Procedure

Prepared from methyl 3-dimethylamino-5-(methylthio)benzo[b]thiophene-2-carboxylate by reaction with lithium amide as described in Example 19. Purification of the crude product by flash chromatography (silica gel, elution with 30% ethyl acetate in hexane) gives 64% of product; mp=140°-142° C.

Workup

  1. customPurification of the crude product
  2. washby flash chromatography (silica gel, elution with 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7857070c950747879c9bcfc79a032e5e
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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